US4477625A - One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions - Google Patents

One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions Download PDF

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US4477625A
US4477625A US06/481,528 US48152883A US4477625A US 4477625 A US4477625 A US 4477625A US 48152883 A US48152883 A US 48152883A US 4477625 A US4477625 A US 4477625A
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radicals
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formula
scavenger
mixtures
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Thomas P. Lockhart
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General Electric Co
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General Electric Co
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Assigned to GENERAL ELECTRIC COMPANY, A CORP. OF N.Y. reassignment GENERAL ELECTRIC COMPANY, A CORP. OF N.Y. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: LOCKHART, THOMAS P.
Priority to US06/481,528 priority Critical patent/US4477625A/en
Priority to GB08328629A priority patent/GB2137647A/en
Priority to CA000450397A priority patent/CA1253278A/en
Priority to DE19843411716 priority patent/DE3411716A1/de
Priority to FR8404996A priority patent/FR2546896A1/fr
Priority to JP59063450A priority patent/JPS59213762A/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/901—Room temperature curable silicon-containing polymer

Definitions

  • RTV room temperature vulcanizable
  • Ceyzeriat U.S. Pat. No. 3,133,891 and Bruner, U.S. Pat. No. 3,035,016, are based on the use of methyltriacetoxysilane with a silanol-terminated polydimethylsiloxane under substantially anhydrous conditions.
  • the one-package compositions of Bruner or Ceyzeriat upon exposure to atmospheric moisture, provide satisfactory one-package room temperature vulcanizable organopolysiloxane compositions exhibiting satisfactory tack-free time, for example, 30 minutes or less after an extended shelf period, the acetic acid by-product is corrosive and has a disagreeable odor.
  • a non-corrosive two package moisture curable organopolysiloxane composition free of carboxylic acid generating groups is shown by Nitzsche et al, U.S. Pat. No. 3,127,363 which is based on the use of a polyalkoxysilane, or polysilicate cross linking agent, in place of methyltriacetoxysilane.
  • the ingredients of the two package noncorrosive composition of Nitzsche et al, are mixed under atmospheric conditions and the resulting composition must be used soon after the ingredients are mixed because the resulting blend has a short shelf life.
  • Nitzsche et al which is typically polyalkoxysilane, silanol-terminated polydiorganosiloxane and tin soap catalyst, provides upon mixing, a fast curing non-corrosive room temperature vulcanizable composition
  • the Nitzsche et al mixture does not have the extended shelf life advantage of the one package system which is required for various commercial uses and therefore is excluded from a variety of applications.
  • Nitzsche et al U.S. Pat. No. 3,065,194, teaches that a mixture of an endblocked dimethylsiloxane polymer, such as hydroxy and alkoxy endblocked, inert filler, ethylorthosilicate and dibutyltindilaurate can be vulcanized upon contact with water, after a 14 day shelf period at room temperature.
  • an endblocked dimethylsiloxane polymer such as hydroxy and alkoxy endblocked, inert filler, ethylorthosilicate and dibutyltindilaurate
  • the various ingredients of the mixture have to be vigorously dried by heating for 1 hour at 200° C., and the RTV, after a relatively short shelf period, has to be drenched with water.
  • Brown et al employed a polyalkoxy end blocked polysiloxane which was based on the use of a mineral acid generating polyalkoxyhalosilane, and a curing catalyst. However, these compositions were found to be unusable because they failed to cure in contact with a tin catalyst, even in the presence of moisture.
  • the term "stable" as applied to the one package alkoxy-terminated organopolysiloxane RTV's of the present invention means a moisture curable mixture capable of remaining substantially unchanged while excluded from atmospheric moisture and which cures to a tack-free elastomer after an extended shelf period.
  • a stable RTV also means that the tack-free time exhibited by freshly mixed RTV ingredients under atmospheric conditions will be substantially the same as that exhibited by the same mixture of ingredients exposed to atmospheric moisture after having been held in a moisture resistant and moisture-free container for an extended shelf period at ambient conditions, or an equivalent period based on accelerated aging at an elevated temperature.
  • the RTV composition of U.S. Pat. No. 4,395,526 further utilize a silicon-containing scavenger for materials having chemically combined hydroxy radical.
  • the silicon containing scavengers can be silanes included within the formula, ##STR3## where R 1 and R 2 are as previously defined, X is a hydrolyzable leaving group selected from amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals, b is a whole number equal to 0 or 1, and c is an integer equal to 1 to 4 inclusive and the sum of b+c is equal to 1 to 4 inclusive.
  • the present invention is based on the discovery that certain organo nitrogen compounds, for example di-t-butylethylenediamine (DBEDA) and certain cyclic amidines having at least one chemically combined unit of the formula, ##STR4## where the free valences of such unit are satisfied by atoms selected from hydrogen, carbon, silicon and mixtures thereof are highly efficient curing accelerators.
  • DBEDA di-t-butylethylenediamine
  • cyclic amidines having at least one chemically combined unit of the formula, ##STR4## where the free valences of such unit are satisfied by atoms selected from hydrogen, carbon, silicon and mixtures thereof are highly efficient curing accelerators.
  • cyclic amidines as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
  • organo nitrogen compounds have been found to provide a dramatic increase in RTV cure rates when used in combination with a condensation catalyst and either a silicon containing scavenger, or silicon-free organic scavenger, as defined hereinafter as compared to conventional amine accelerators such as di-n-hexylamine.
  • organo nitrogen curing accelerators of the present invention can be utilized in further combination with organic amines, such as di-n-hexylamine, to achieve further acceleration in cure rate.
  • RTV compositions of the present invention cross-linking polyalkoxysilane having the formula, ##STR5## where R 1 , R 2 and b are as previously defined.
  • RTV compositions are provided which are stable over an extended period of time and which are convertible upon exposure to atmospheric moisture to the tack-free state in a substantially reduced period of time.
  • a one-package, substantially anhydrous, room temperature vulcanizable organopolysiloxane composition stable under ambient conditions in the substantial absence of moisture over an extended period of time and convertible to a substantially acid-free, tack-free elastomer comprising by weight,
  • an organic material having at least one alcohol reactive functional groups which is suitable as a scavenger for hydroxy radicals and which has a molecular weight in the range of from about 40 to about 1,000 and consists essentially of a mixture of chemically combined atoms selected from C, H, N, O, P, S, Cl, F, Br and I and
  • X is as previously defined, d is a whole number equal to 0 to 4 inclusive, and the remaining valences of Si other than those which can be satisfied by X can be satisfied by atoms selected from Si, H, C, O, N, P, S, transition elements IIIa, IVa, Va, VIa, VIIa and VIII and mixtures thereof, and
  • Radicals included within R of formulas (1) and (2) are, for example, aryl radicals and halogenated aryl radicals, such as phenyl, tolyl, chlorophenyl, naphthyl; aliphatic and cycloaliphatic radicals, for example, cyclohexyl, cyclobutyl; alkyl and alkenyl radicals, such as methyl, ethyl, propyl, chloropropyl, vinyl, allyl, trifluoropropyl; and cyanoalkyl radicals, for example, cyanoethyl, cyanopropyl, cyanobutyl.
  • aryl radicals and halogenated aryl radicals such as phenyl, tolyl, chlorophenyl, naphthyl
  • aliphatic and cycloaliphatic radicals for example, cyclohexyl, cyclobutyl
  • alkyl and alkenyl radicals such as
  • Radicals preferably included within R 1 are, for example, C.sub.(1-8) alkyl radicals, for example, methyl, ethyl, propyl, butyl, pentyl; C.sub.(7-13) aralkyl radicals, for example, benzyl; phenethyl; alkylether radicals such as 2-methoxyethyl; alkylester radicals, for example 2-acetoxyethyl; alkylketone radicals, for example 1-butan-3-onyl; alkylcyano radicals, for example 2-cyanoethyl.
  • Radicals included within R 2 are the same or different radicals included within R radicals. In formulas (1-3), where R, R 1 , and R 2 , can be more than 1 radical, these radicals can be the same or different.
  • the organo nitrogen accelerators utilized in the practice of the present invention are commercially available.
  • a method for making the di-t-butylethylene diamine is shown by Webb, U.S. Pat. No. 4,160,705, assigned to the same assignee as the present invention.
  • the cyclic amidines are shown in the Chemistry of Amidines and Amidate, S. Patai, (1975), pp. 283-348, John Wiley & Sons, New York.
  • the amidines which can be used in the practice of the present invention are material included within the following formula, ##STR6## where R 3 -R 6 can be selected from C.sub.(1-8) alkyl and alkenyl radicals and C.sub.(6-13) aryl radicals.
  • R 4 and R 5 , or R 3 and R 4 can be part of a cyclo alkylene structure.
  • R 3 -R 6 can include silicon atoms whose valences can be satisfied by monovalent or polyvalent organic radicals.
  • cross-linking polyalkoxysilanes included within formula (5) are, for example, methyltrimethoxysilane; methyltriethoxysilane; ethyltrimethoxysilane; tetraethoxysilane; vinyltrimethoxysilane; etc.
  • organic scavengers which can be used in the practice of the present invention in combination with the above-described organo nitrogen accelerators are, for example, alkenyl carboxylates, such as isopropenyl acetate, vinyl acetate, but-2-ene-3-yl acetate, isopropenyl propionate and vinyl propionate.
  • organic scavengers include organic acyl stabilizers, such as acetic anhydride, benzoyl anhydride, ketenes, for example, diphenyl ketene, lactones such as methylene butyrolactone, beta-butyrolactone, and epsilon-caprolactone; vinyl ethers such a 4,5-dihydro-2-methylfuran, and carbodiimide derivatives such as cyclohexylcarbodiimide.
  • organic acyl stabilizers such as acetic anhydride, benzoyl anhydride, ketenes, for example, diphenyl ketene, lactones such as methylene butyrolactone, beta-butyrolactone, and epsilon-caprolactone
  • vinyl ethers such a 4,5-dihydro-2-methylfuran
  • carbodiimide derivatives such as cyclohexylcarbodiimide.
  • silane scavengers for chemically combined hydroxy radicals included within formula (3) are, for example,
  • Oximatosilanes such as,
  • Carbamatosilanes such as,
  • Aminosilanes such as,
  • Amidosilanes such as,
  • Imidotosilanes such as,
  • Ureidosilanes such as,
  • Isocyanatosilanes such as,
  • silanes are, for example, methyltris(N-methylacetamido)-silane; tetra(isopropenoxy)silane. Also included are silane having different leaving groups such as diethylamino(N-methylcarbamato)isopropenoxy(N-allyl-N',N'-dimethylureido) silane.
  • silicon containing scavengers having a functional unit of formula (3) silazanes which are more particularly described in the copending application of John J. Dziark, now U.S. Pat. No. 4,147,042, filed Feb. 17, 1982, incorporated herein by reference.
  • Some of these silicon-nitrogen containing scavengers can be more particularly defined as a member selected from:
  • zeolites which are shown in copending application Ser. No. 481,529, filed concurrently herewith and incorporated herein by reference. Some of these zeolites, or molecular sieves are shown in Reagents for Organic Synthesis, L. F. Fieser and M. Fieser, John Wiley, New York 1967), pages 703-705, Vol. 1. More particularly, molecular sieves are synthetic zeolites of completely regular crystal structure and uniform pore size.
  • Typical molecular sieves which can be utilized are shown by types 3A, 4A, 5A and 13X which are available as powder, 1/16" pellets and 1/8" pellets, or in certain instances available in beads in three sizes. The following shows the compositions of some of these materials.
  • silane scavengers there are also included within the scope of the present invention silicon containing scavengers as shown in the aforementioned copending application Ser. No. 476,000, filed Mar. 17, 1983 for Swiger et al, such as ##STR9##
  • the alkoxy-terminated organopolysiloxane of formula (2) can be made by various procedures.
  • One procedure is taught by Cooper et al U.S. Pat. No. 3,542,901 involving the use of a polyalkoxysilane with a silanol-terminated polydiorganosiloxane in the presence of an amine catalyst.
  • a cross-linking silane of formula (3) can be used in accordance with Cooper et al's method to end-cap a silanol-terminated polydiorganosiloxane of formula (1).
  • silanol-terminated polydiorganosiloxanes which can be used to make the polyalkoxyorganopolysiloxanes are well known and preferably have a viscosity in the range of from about 100 to about 400,000 centipoise and more preferred from about 1000 to about 250,000 centipoise when measured at about 25° C.
  • These silanol-terminated fluids can be made by treating a higher molecular weight organopolysiloxane, such as dimethylpolysiloxane with water in the presence of a mineral acid, or base catalyst, to tailor the viscosity of the polymer to the desired range.
  • cyclopolysiloxane such as octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, or mixtures thereof, will also provide for higher molecular weight polymers.
  • such polymers are decatalyzed of equilibration catalyst by standard procedures prior to use, such as shown by Boot U.S. Pat. No. 3,153,007, assigned to the same assignee as the present invention.
  • Silanol-terminated organopolysiloxanes having viscosities below 1200 centipoises can be made by treating organopolysiloxanes consisting essentially of chemically combined diorganosiloxy units with steam under pressure.
  • Other methods that can be employed to make silanol-terminated polydiorganosiloxanes are more particularly described in U.S. Pat. No. 2,607,792 to Warrick and U.K. Pat. No. 835,790.
  • Effective amounts of the condensation catalysts which can be used in the practice of the present invention to facilitate the cure of the RTV compositions are, for example, 0.001 to 1 part based on the weight of 100 parts of the silanol-terminated polydiorganosiloxane of formula (1).
  • tin compounds for example, dibutyltindilaurate; dibutyltindiacetate; dibutyltindimethoxide; carbomethoxyphenyl tin tris-uberate; tin octoate; isobutyl tin triceroate; dimethyl tin dibutyrate; dimethyl tin di-neodeconoate; triethyl tin tartrate; dibutyl tin dibenzoate; tin oleate; tin naphthenate; butyltintri-2-ethylhexoate; tinbutyrate.
  • the preferred condensation catalysts are tin compounds and dibutyltindiacetate is particularly preferred.
  • Titanium compounds which can be used are, for example, 1,3-propanedioxytitanium bis(ethylacetoacetate); 1,3-propanedioxytitanium bis(acetylacetonate); diisopropoxytitanium bis(acetylacetonate); titanium naphthenate; tetrabutyltitanate; tetra-2-ethylhexyltitanate; tetraphenyltitanate; tetraoctadecyltitanate; ethyltriethanolaminetitanate.
  • beta-dicarbonyltitanium compounds as shown by Weyenberg U.S. Pat. No. 3,334,067 can be used as condensation catalysts in the present invention.
  • Zirconium compounds for example, zirconium octoate, also can be used.
  • metal condensation catalysts are, for example, lead 2-ethyloctoate; iron 2-ethylhexoate; cobalt 2-ethylhexoate; manganese 2-ethylhexoate; zinc 2-ethylhexoate; antimony octoate; bismuth naphthenate; zinc naphthenate; zinc stearate;.
  • nonmetal condensation catalysts examples include hexylammonium acetate and benzyltrimethylammonium acetate.
  • fillers and pigments can be incorporated in the silanol or alkoxy-terminated organopolysiloxane, such as for example, titanium dioxide, zirconium silicate, silica aerogel, iron oxide, diatomaceous earth, fumed silica, carbon black, precipitated silica, glass fibers, polyvinyl chloride, ground quartz, calcium carbonate etc.
  • the amounts of filler used can obviously be varied within wide limits in accordance with the intended use. For example, in some sealant applications, the curable compositions of the present invention can be used free of filler.
  • the filler can consist of a major amount of extending materials, such as ground quartz, polyvinylchloride, or mixtures thereof, preferably having an average particle size in the range of from about 1 to 10 microns.
  • compositions of the present invention also can be employed as construction sealants and caulking compounds.
  • the exact amount of filler therefore, will depend upon such factors as the application for which the organopolysiloxane composition is intended, the type of filler utilized (that is, the density of the filler and its particle size).
  • a proportion of from 10 to 300 parts of filler which can include up to about 35 parts of a reinforcing filler, such as fumed silica filler, per 100 parts of silanol-terminated organopolysiloxane is utilized.
  • the room temperature vulcanizable compositions can be made by agitating, for example stirring, a mixture of materials which can consist of the alkoxy-terminated polydiorganosiloxane, organic scavenger, or silane scavenger of formula (3), or mixture thereof, cross-linking silane of formula (5) which can be optional, an organo nitrogen accelerator where the blending is performed in the substantial absence of atmospheric moisture. Thereafter, the condensation catalyst can also be added in the substantial absence of atmospheric moisture.
  • moisture-free conditions and “substantially anhydrous conditions”, with reference to making the RTV compositions of the present invention, mean mixing in a dry box, or in a closed container which has been subjected to vacuum to remove air, which thereafter is replaced with a dry inert gas, such as nitrogen.
  • Temperatures can vary from about 0° C. to about 180° C. depending upon the degree of blending, the type and amount of filler.
  • a preferred procedure for making the RTV compositions of the present invention is to agitate under substantially anhydrous conditions, a mixture of the polyalkoxy terminated organopolysiloxane, filler, along with an amount of polyalkoxysilane of formula (5) sufficient to effect the substantial elimination of hydroxy functional groups in the mixture.
  • a stabilizing amount scavenger for hydroxy radicals in accordance with the practice of the present invention means that there can be used from about 0.1 to about 10 parts of scavenger per 100 parts of the alkoxy-terminated polydiorganosiloxane or the silanol terminated polydiorganosiloxane.
  • scavenger preferably 1 or 2 parts per 100 parts of organopolysiloxane polymer.
  • This "end-capping" procedure can require several minutes, hours, or even days, depending upon such factors as the amount of silanol on the filler, the nature of the OR 1 radical on the cross-linking silane, etc.
  • condensation catalyst, cross-linking silane or mixture thereof can be added to the substantially silanol-free mixture the condensation catalyst, cross-linking silane or mixture thereof, along with other ingredients, for example, the curing accelerator and pigments.
  • a room temperature vulcanizable, one-package polydimethylsiloxane composition was prepared in the absence of moisture utilizing a methyldimethoxysiloxy terminated polydimethylsiloxane having a viscosity of about 15-30 ⁇ 10 3 centipoise at 25° C., dibutyltindiacetate and an effective amount of an organo nitrogen accelerator as provided in the practice of the present invention.
  • the RTV composition was prepared in an inert atmosphere under substantially anhydrous conditions and samples of the composition were removed and placed in aluminum pans to determine their tack-free times (TFT) in a 58% humidity chamber at room temperature.
  • TFT tack-free times
  • Example 1 The procedure of Example 1 was repeated, except that additional RTV compositions were prepared utilizing methyldimethoxy-terminated polydimethylsiloxane having a viscosity of about 15-30 ⁇ 10 3 centipoise at 25° C. (composition A) and the RTV composition as shown in Example 1 (composition B).
  • RTV compositions were prepared following the procedure of Example 1 utilizing di-t-butylethylenediamine as an organo nitrogen accelerator.
  • the above RTV compositions also contained an organic scavenger such as beta-butyrolactone and epsilon-caprolactone or silane scavenger such as methyldimethoxyisopropenoxysilane.
  • the RTV composition employing silane scavenger methyldimethoxyisopropenoxysilane used a methyldimethoxy chain-stopped polymer having a viscosity of about 150-200,000 centipoise at 25° C.
  • silane scavenger containing RTV composition a trimethylsiloxy stopped polydimethylsiloxane fluid having a viscosity of 50 centipoise.
  • the RTV compositions containing the organic scavengers were prepared by blending together under substantially anhydrous conditions, 100 parts of a methyldimethoxy-terminated polydimethylsiloxane having a viscosity of 15-30 ⁇ 10 3 centipoise at 25° C., 0.2 part of dibutyltindiacetate, 0.3 part of di-t-butylethylenediamine and 2 parts of scavenger.
  • the RTV composition containing the silane scavenger was prepared by blending under substantially anhydrous condition, 63 parts of the methyldimethoxy-terminated polydimethylsiloxane, 37 parts of the polydimethylsiloxane fluid having terminal trimethylsiloxy units, 0.2 part of dibutyltindiacetate, 0.3 part of the di-t-butylethylenediamine and 2 parts of silane scavenger.
  • silanol terminated polydiorganosiloxane of formula (1) is used with silicon containing scavenger of formula 3
  • silicon containing scavenger of formula 3 there can be used 0.001 part to 1 part of polyalkoxysilane, per part of silanol polymer.

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US06/481,528 1983-04-01 1983-04-01 One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions Expired - Fee Related US4477625A (en)

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Application Number Priority Date Filing Date Title
US06/481,528 US4477625A (en) 1983-04-01 1983-04-01 One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions
GB08328629A GB2137647A (en) 1983-04-01 1983-10-26 One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions
CA000450397A CA1253278A (en) 1983-04-01 1984-03-23 One package, stable, moisture curable, alkoxy- terminated organopolysiloxane compositions
DE19843411716 DE3411716A1 (de) 1983-04-01 1984-03-29 Stabile, feuchtigkeitshaertbare, einkomponenten-alkoxyendgruppen-aufweisende organopolysiloxan-massen
FR8404996A FR2546896A1 (fr) 1983-04-01 1984-03-30 Composition d'organopolysiloxane a terminaisons alcoxy vulcanisable a froid, en une partie et procede de preparation
JP59063450A JPS59213762A (ja) 1983-04-01 1984-04-02 ワンパツケ−ジ型の安定な湿気硬化性アルコキシ−終端オルガノポリシロキサン組成物
JP3163435A JPH0593139A (ja) 1983-04-01 1991-06-10 Ｒｔｖオルガノポリシロキサン組成物の製法

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US5741839A (en) * 1995-05-02 1998-04-21 Huels Silicone Gmbh Storage-stable alkoxy-crosslinking RTV1 systems
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FR2882760A1 (fr) * 2005-03-04 2006-09-08 Rhodia Chimie Sa Compositions organopolysiloxanes durcissant en elastomeres des la temperature ambiante en presence d'humidite
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US20100063215A1 (en) * 2006-12-25 2010-03-11 Kaneka Corporation Curable composition
US20100286344A1 (en) * 2008-02-22 2010-11-11 Asahi Glass Company, Ltd. Curable composition
US9617373B2 (en) * 2015-02-13 2017-04-11 LCY Chemical Corp. Curable resin composition, article, and method for fabricating the same
US9944770B2 (en) 2013-06-20 2018-04-17 Momentive Performance Materials Inc. Moisture curable compound with thiourea
US20180171082A1 (en) * 2015-04-16 2018-06-21 Sika Technology Ag Catalyst containing amidine groups
CN109777342A (zh) * 2018-12-29 2019-05-21 江苏创景科技有限公司 一种用于双组分有机硅灌封胶的固化促进剂及其应用

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US4472564A (en) * 1983-04-01 1984-09-18 General Electric Company Method for making an enoxy stabilized room temperature vulcanizable organopolysiloxane composition which resists color change upon aging
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JPH0455460B2 (enrdf_load_stackoverflow) 1992-09-03
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CA1253278A (en) 1989-04-25

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